Use of oxazoline flavoring agents and flavor extenders

ABSTRACT

A series of novel 2,4,5-alkyl-substituted 3-oxazolines and their use as flavoring agents and flavor extenders. The use of 2,5dialkyl-2-oxazolines as flavoring agents and flavor extenders.

United States Patent [191 Hetzel et al.

[451 July 1,1975

[ USE OF OXAZOLINE FLAVORING AGENTS AND FLAVOR EXTENDERS [75] Inventors: Donald S. Hetzel, New London;

Anibal Torres, Waterford, both of Conn.

[73] Assignee: Pfizer Inc., New York, N.Y.

[22] Filed: June 29, 1973 [21] App]. No.: 374,931

Related US. Application Data [60] Division of Ser. No. 150,768, June 7, 1971, Pat. No. 3,769,293, which is a continuation-in-part of Ser. No. 34,876, May 5, 1970, abandoned.

[52] U.S. Cl 426/536; 426/537 [51] Int. Cl A23l 1/26 [58] Field of Search 426/65, 175; 260/307 F Primary Examiner.loseph M. Golian Attorney, Agent, or Firm-Connolly and Hutz [5 7] ABSTRACT A series of novel 2,4,5-alkyl-substituted 3-0xazolines and their use as flavoring agents and flavor extenders. The use of 2,5-dialkyl-2-oxazolines as flavoring agents and flavor extenders.

3 Claims, No Drawings 1 I USE OF OXAZOLINE FLAVORING AGENTS AND FLAVOR EXTENDERS CROSS REFERENCE TO RELATED APPLICATION The present application is a division of application Ser. No. l50,768 filed June 7, l97l, now US. Pat. No. 3,769,293, which in turn is a continuation-impart of application Ser. No. 34,876 filed May S, 1970, and now abandoned. I

BACKGROUND OF THE INVENTION This invention relates to a series of novel 2,4,5-alkylsubstituted 3-oxazolines which are useful as flavoring agents and flavor extenders. It further relates to the use of certain known 2,5-dialkyl-2-oxazolines as flavoring agents and flavor extenders.

Artificial flavoring agents and flavor enhancers are widely used today and number in the hundreds. A wide variety of chemical compounds, especially organic compounds, are used for these purposes and include aliphatic and aromatic alcohols, aldehydes, ketones, acids, esters, phenols, and lactones. Certain compounds are known to have a specific kind of taste and aroma comparable in many instances to that of a naturally occurring product. For example, 'y-undecalactone, known as peach aldehyde, is used as an artificial flavoring agent in the manufacture of products hav ing a peach-like flavor. The use of such compounds by flavor technologists provides a means of simulating natural flavors and aromas by solely artificial means.

Other compounds, usually referred to as flavor enhancers or extenders are effective in intensifying the sensory response to flavor materials in a manner analogous to the action of a chemical catalyst, or as augmentors or suppressors of the responses (odor, taste, and mouthfeel) of sensory organs to the stimuli of food. They are effective at low levels and add little or no flavor of their own at these levels; Flavor extenders may be present as normal constituents of a food, or may be produced in the processing. At its inception the definition of flavor extenders or enhancers applied only to products which had this effect without contributing their own distinctive flavors. Today there is a tendency to broaden this definition to include as extenders products which do contribute some flavor. In many cases, the artificial flavor compositions, often including enhancers, are preferred because of their stability, availability, and lower cost.

Artificial flavoring agents and flavor enhancers are widely used in foodstuffs and beverages and in increasing the acceptability of medicines where, for example, they are added to tablet coatings and elixirs.

SUMMARY OF THE INVENTION This invention comprises novel compounds having the formulae:

and I I Wherein R R R, and R are eachalkyl groups containing up to 6 carbon atoms, and R and R are each alkyl groupscontainin'g from 2 to 6 carbon atoms.

This invention also comprises a nieth'odfor flavoring foodstuffs and'medicine's which comprises incorporating therein one of the novel compounds given above or one of the known compounds of the formulae:

H II

II CH wherein R is an alkyl group containing up to 6 carbon atoms.

DETAILED DESCRIPTION OF THE INVENTION The novel compounds of the present invention are readily prepared by the condensation of the appropriately substituted a-ketol and aldehyde with ammonia in aqueous solution at room temperature. The alkyl substituents at the 4,5-positions of the 3-oxazoline are derived from the a-ketol, while the alkyl moiety of these compounds at the 2-position are derived from the aldehyde. 3-oxazolines containing alkenyl and aryl substituents at the 2-, 4-, and 5-positions can also be prepared by this method using the appropriately substituted precursors. The reaction proceeds quite smoothly and after stirring the reactants at room temperature for several hours the 3-oxazoline is extracted with ether. After drying and evaporating the ether extracts the products can be purified by fractional distillation, generally under vacuum. If desired, they can be purified further by means of gas-liquid chromatography.

The known compounds of this invention are prepared by methods described in the literature (J. Am. Chem. Soc. 57:1079, 1935).

The compounds described herein exhibit unique flavor and odor notes which make them useful for flavoring beverages, confections and foodstuffs and imparting desirable notes to perfumes and cosmetics. In addition, it has been found that the herein described compounds are effective as flavor and aroma enhancers for foodstuffs.

We have discovered that the higher homologs of the herein described compounds are significantly more effective as flavor and aroma enhancers than the lower lower homologs and impart a smoother and more desirable aroma and flavor to foodstuffs. Thus, the cocoalike flavor of 2-isopropyl-4,5-diethyl-3-oxazoline is about five-times more intense than the previously reported 2-isopropyl-4,5-dimethyl-3-oxazoline.

In the case of the known 2,5-dialkyl-2-oxazolines, a S-methyl substituent does afford preferred products,

but in somewhat analogous fashion, extending the carbon chain at the 2-position intensifies flavoring potency. Thus, the strawberry-like flavor and aroma of 2-nbutyl-5-methyl-2-oxazoline is muchmore intense than the horseradishdike taste and aroma of the 2,5- dimethyl compound.

The 2,4,5,5-tetraalkyl-3-oxazolines also possess valuable flavoring characteristics and impart pleasing flavor notes when added to foodstuffs and the like.

Many of the novel compounds of the present invention have individual and unique flavoring properties. The 2-isopropyl-4,5-diethyl compound has a strong cocoa-like odor and flavor. This compound can be used to prepare artificial cocoa-flavored products and has been used with other additives and compounded with soy proteins and dextrose to give a chocolate drink formulation very similar in appearance, taste and odor to products made with natural chocolate derivatives. Soy proteins are present in soybean oil meal and soybean cake, and because of their availability and low cost they have been advocated as food supplements in areas of the world which suffer from protein deficiencies. Unfortunately, the taste of these crude soy proteins is somewhat unpleasant. It can be seen that the use of 2- isopropyl-4,5-diethyl-3-oxazoline to prepare an acceptable cocoa-tasting protein beverage is potentially of great importance. Indeed, inexpensive, pleasant-tasting high protein beverages are being widely used throughout various parts of the world as a means of providing supplemental amounts of protein in the diet, particularly for children.

This compound can be used as a flavor extender with natural and synthetic cocoa and chocolate bases. By a flavor extender is meant a constituent which either improves the natural flavor, i.e., a flavor enhancer, or when used to replace a portion of a natural flavoring material permits one to still obtain the same overall flavoring effect. Thus, it has been found that addition of up to 5 ppm of 2-isopropyl-4,5diethyl 3-oxazoline to a commercial cocoa base improves the aroma. We generally prefer to use about 1-100 ppm of the instant compounds for flavoring effects in foodstuffs.

The various other members of the novel series of compounds of the present invention also possess interesting odors. 2-Isopropyl-4,5-di-n-propyl 3-oxazoline has a banana-like odor. While 2-t-butyl-4,5,S-trimethyl 3-oxazoline has a cool minty odor, it has been found that in low concentrations it can be used in preparing synthetic strawberry flavors as well as synthetic banana flavors and butter flavors.

The series of known compounds of this invention also possess interesting flavors and aroma. In addition to the two compounds previously mentioned, 2-ethyl-5-methyl-2-oxazoline has a fruity, melon-like aroma and taste potentially useful in enhancing rum or caramel flavored products such as rum punch beverage or the like. The 2-n-propyl-5-methyl compound has a cool, minty flavor and aroma, and the 2-n-pentyl-5-methyl compound has a fruity, sweet flavor and aroma, both potentially useful in flavoring or enhancing the flavors of a variety of comestibles.

The herein described compounds can also be compounded in various perfume and cosmetic compositions to give a limitless variety of fragrances, the type depending upon the skill and ingenuity of the formulator. Generally a range of from about l-200 ppm gives the best results. These compounds can also be used in flavoring medicaments, in particular to tablet coatings and in the preparation of elixirs.

The following examples are given to illustrate further the scope of the present invention and are not to be construed as limitations thereof.

EXAMPLE l 11.6 g. (0.10 moles) of propionoin and 7.2 g. (0.10 moles) of isobutyraldehyde are added to ml. of ammonium hydroxide. The reaction mixture is stirred at room temperature for 6 hours. The reaction mixture is extracted several times with diethyl ether, the extracts are combined, and dried over anhydrous sodium sulfate. After filtering and evaporating the ether, the residue is distilled through a short Vigreaux column under reduced pressure. The fraction boiling at 90-l00C./33 mm is collected to yield 12.4 g. (74%) of 2-isopropyl-4,5-diethyl-3-oxazoline. The pure material has a sharp cocoa-like odor.

The 3-oxazolines listed in the table below are also prepared from the indicated starting materials according to the above procedure.

Starting Materials Acyloin Aldehyde Product B.P. C. Odor C H COCHOHC H C H CHO 2,4.5-triethyl- 96-l04/33 mm weedy 3-oxazoline C H -,COCHOHC- H.-, ZTIESM 2-s-butyll09/l5 mm cocoa 4.5-diethyl-3- Oxazoline n-C,.H,CO- i-C,.H Z-i-propyl- 96l25 mm cool-banana CHOHnCHHT CHO 4.5-di-npropyl-3- oxazoline CH=iCOC(CH=|)OHCH,-i 2-i-propyl- 75/30 mm cool menthol;

' 4,5.5-trimethylunroasted 3-oxazoline cocoa CH,,COC(CH )OHCH=, iCTICdH Z-i-butylllO-l l3/30 mm earthy;

4.5.5-trimethyldiacctyl 3-o'xazoline CH= COC(CH.1)OHCH t-C HHCHO Z-t-butyl- 7()/25 mm cool-minty I 4.5.5-trimcthyl- 3-oxazolinc The compounds listed below are also prepared aecording to the above procedure.

i asa EXAMPLE 1]] Comparison of Flavor Intensity and Quality of 2,4,5-Trimethyl-3-Oxazo1ine with 2-Methyl-4,5-Diethyl-3 Oxazoline An organoleptic evaluation was conducted to compare the flavor (odor and taste) intensity and quality.

between 2,4,5-trimethyl-3-oxazoline and 2-methyl-4,5- diethyl-3-oxazoline in 5% sugar-aqueous solution. Both test materials were examined at the same concentrations according to the protocol below.

Thirteen samples of the 5% sugar-aqueous solution were prepared comprising six samples containing re 8 The results of the aboveflavo r comparison show the flavor of 2-methyl-4;5-diethyl-3-o xazoline to be strongerthan thatofZ,4,5-trimethyl-3-oxazoline. Moreover, the results show that the flavor imparted by the 2- 5 methyl-4,5-diethyl-3-oxazoline is different in character than that of 2,4,5-trimethyl-3-oxazoline. The former compound imparted a sweeter, delicate and more appealing'flavor than the 2,4,5-trimethyl-3-oxazoline.

EXAMPLE IV 5 Sensory Evaluation and Comparison of Fl'avor Intensity and Quality of 2-Isopropyl-4,5-diethyl-3-oxazoline with 2 -lsopropyl-4,S-Dimethyl-3-oxazoline The flavor intensity and character of 2-isopropyl-4,5- diethyl-3-oxazoline were-evaluated and compared with 2-isopropyl-4,5-dimethyl-3-oxazoline in 5% sucroseaqueous solution. Two series of test solutions were prepared. Test series I consisted of four samples containing respectively 50, 25, 1Q andl part per million of 2- isopropyl-4,5-diethyl-3-oxazoline. Test series ll consisted of four samples to which was added separately 50, 25,210, and 1 part per million of 2-isopropyl-4,5- dimethyl-S-oxazoline. The solutions were cooled and evaluated by two judges as to odor and taste (flavor) by arranging them in decreasing order of flavor intensities. At the same time the solutions flavor qualities were also Coded Solutions Compound Concentration in ppm S 2.4.5-Trimethyl-3oxazoline 1,000 P 2.4.5-Trimethyl-3-oxazoline 500 N 2.4.5-Trimethyl-3-oxazoline 200 Y A 2 .4.5-Trimethyl-3-oxazolinc 100 i K 2.4.5-Trimethyl-3-oxazoline D 2.4.S-Trimethyl-S-oxazoline 25 B 2-Methyl-4.5Dielhyl-3-oxazoline 1.000 J 2-Mcthyl-4.5-Diethyl-3-oxazoline 500 T 2-Methyl-4,5-Diethyl-3oxazoline 200 E 2-Methyl-4.S-Diethyl-B-oxazoline R 2-Methyl-4.5-Diethyl-3-oxazoline 50 O Z-Methyl-4.5-Diethyl-3-oxazoline 25 Z 5% Sugar Solution (Control) Evaluation 1: Order in which judges arranged solution in decreasing order of flavor intensity and quality. H Judges Decreasing Order of Flavo Judges Remarks Intensities B, J. T. E and R exhibit similar flavor character described as green-sweet" reminiscent of freshly cut snap beans.

notes.

B. 5.1. R E, R. A. K.Z

B, J, T, E impart a sweeten green delicate flavor while S. P. N. A exhibited a rougher flavor character."

compared. The results of their sensory flavor evaluation have been outlined below.

Coded Concentration in Solution Compound Parts Per Million No. 14 2-Isopropyl-4.5-diethyl-3-oxazoline 50 26 2-1sopropy1 4.5-diethy13-oxazo1ine 33 2-1sopropy1-4.5-diethy1-3-oxazo1ine 1O 7 21sopropy1-4.5-diethy1-3oxazo1ine l 4 2-1sopropy1-4.5-dimethy1-3oxazo1ine 50 13 21sopropyI-4.5-dimcthyl-3-oxazoline 25 8 2-Isopropy14,5-dimethyl-3-oxazoline 10 5 2-Isopropyl-4.5-dimethy1-3-oxa2oline l Judges Decreasing Order of Flavor Intensities Judges Remarks I 14. 26. 33 8; 4 (comparable). 13. 8. 14. 26. 33 and 7.exhibit 7. 5 a strong. sweet cocoa-like flavor with mild green-like notes; while 4. 13. band 5 emparted a strong greenfungal weedy-like flavor with weak cocoa notes.

2 I4. 26. 4. 33. 13. 7. S. 5 14.26. 33 and 7 exhibit a pronounced sweet cocoa flavor. 4. 13. 8 and 5 impart a different flavor. rougher in character and not as desirable.

Based on the above results the flavor intensity of 2- 25 4,5-diethyl-3oxazoline exhibited an aroma and taste isopropy1-4,5-diethy1-3-oxazo1ine was rated about 5 times more intense than the flavor of 2-isopropy1-4,5- dimethy1-3-oxazoline. The above results also show that 2-isopropy1-4,5-diethy1-3-oxazoline imparted a flavor which was dramatically recognized as strongly sweet cocoa-like while the flavor" of the 2-isopropy1-4,5- dimethyl was judged rougher in character possessing a strong green-fungal odor with a less intense cocoa-like flavor. EXAMPLE V The chocolate-flavored formulations below are prepared from the indicated ingredientsz Chocolate Flavors enhancement substantially superior to milk samples prepared from flavor formulation B. which did not contain this compound. In addition, the flavor exhibited by products made with formulation Awere more natural and the taste smoother than those made with formulation B.

EXAMPLE VI oxazoline to chocolate-flavored bakers products and chocolate-flavored confectionary products (either flavored with natural cocoa powders, cocoa extracts, or

Flavor Formulation B Ingredients Flavor Formulation A Weight in Grams Weight in Grams Vanillin 3.0 3.0 Vanitrope 1% in Propylene Glycol 3.0 3.0 Maltol 4% in Propylene Glycol 10.0 10.0 2-1sopropyl4.5-diethy1-3-oxazoline 0.5 Propylene Glycol 73.5 74.0 Cocoa Extract (Anthoine Chiris) 10.0 10.0

Organoleptic evaluation of the above formulations is performed by a panel ofjudges. who compare the aromas and taste of the two flavors in milk drinks. A series of milk samples are prepared with a sufficient amount of beverage formulation A to provide series of samples containing from 1 to parts per million (ppm) of 2- isopropy1-4-,5--diethy1-3 o azo1ine. Another series of milk samples are prepared using an equivalent amount of formulation B. 1 i

In every case it is found that milk samples prepared with flavor formulation A containing the Z-isopropyl- Ingredients Synethetic Banana Flavors Flavor Formulation C Flavor Formulation D Weight in Grams Weight in Grams Ethyl Alcohol U.S.P. Vanillin Orange Oil California U.S.P.

Clove Oil Bourbon Propylene Glycol Amyl Acetate Amyl Valerate Acetaldehyde 2-Isobuty1-4.5 .S-trimcthyIii-oxazoline 10.480 13.480 0.370 0.370 0.066 0.066 0.333 0.333 26.421 26.421 5.000 5.000 3.330 3.330 1.000 1.000 3.000 Totals: 50.000 50.000

Synthetic Strawberry Flavors Flavor Formulation E Flavor Formulation The above flavor formulations are used to prepare a series of gelatin desserts. A sufficient amount of flavor formulations C and E are used to provide samples of 2 dessert containing from 2 to 100 parts per million of 2- isobutyl-4.5,5-trimethyl-3-oxazoline. Controls containing flavor formulations D and F are prepared.

The flavor imparted by the compositions containing 2-isobutyl-4,5,5-trimethyl-3-oxazoline exhibited aroma and taste enhancements substantially superior to the controls (formulations D and F). The flavor imparted by the formulation containing the test compound was judged more natural and the taste smoother and mellower, as compared to samples prepared from the controls.

Similar results are obtained when the remaining compounds listed in Example 1 are used in place of 2- isobutyl-4,5,5-trimethyl-3-oxazoline.

EXAMPLE Vlll Between 2 and 4% by weight of 2-isobutyl-4,5,5- trimethyl-3-oxazoline is blended with the formulation below, sufficient propylene glycol being added to bring total weight of composition to 100 parts.

EXAMPLE 1X When 2 to parts per million of 2-isopropyl-4,5-

diethyl-3-oxazoline is added to conventional peanutflavored products (either those containing natural peanut flavors or those containing both natural and synthetic flavors), products having a more desirable delicate flavor are obtained.

Similar results are obtained with the remaining compounds of Example 1.

EXAMPLE X A cocoa-flavored elixir for pharmaceutical purposes is prepared as indicated below:

2-isopropyl-4.5-diethyl-3-oxazoline 5 gm. Sucrose 650 gm. Liquid Glucose 200 gm. Glycerin 50 ml. Sodium Chloride 1 gm. Vanillin 0.2 gm. Sodium Benzoate 1 gm. Purified Water, a sufficient quantity to make 1000 ml.

Butter Flavor 5O lngredients Parts by Weight Butyric Acid 4.4 Ethyl Butyrate .2 Amy! Butyrate 4.3 Diacetyl 1 l 5 5 Benzyl Alcohol 5.0 Phenoxy Ethyl lsobutyrate 4.3 2-isobutyl-4.5,5-trimethyl-3-oxazoline 2 to 4 propylene glycol q.s. 100

The sucrose and the 2-isopropyl-4,5-diethyl-3- oxazoline are mixed. and to this mixture is gradually added a solution of the liquid glucose, glycerin, sodium chloride, vanillin, and sodium benzoate in 325 ml. of hot purified water. The entire mixture is boiled for 2 minutes and allowed to cool to room temperature. Sufficient purified water is added to make the product measure 1000 ml.

Similar elixirs are prepared by using the other compounds listed in Example 1.

EXAMPLE XI Synthetic strawberry flavors were prepared according to the following formulation, which also contained 2-n-butyl-5-methyl-2-oxazoline at concentration levels of (Control), 0.5%, 1% and 1.5%.

Synthetic Strawberry Flavor by Ingredients weight 3-methyl naphthyl ketone 0.060 Heliotropin 0.020 Nerolin 0.005 Diacetyl 0.020 Dimethyl anthronilate 0.020 Raspberry ketone 1-4 hydroxy-phenyl butanone 3) 0.010 Ethyl methyl phenyl glycidate 0.500 Vanillin 0.500 Ethyl meltol 0.500 Ethyl corproate 0.040 Butyric acid 0050 Ethyl oenawthate 0.010 Aldehyde C 0.010 Cinnamic aldehyde 0.005 Orris concrete 1:16 tincture 0.020

Ethyl Alcohol to bring the total weight to 100% Organoleptic evaluations of the resultant flavor blends were carried out by comparing the treated flavor versus the control on perfume smelling blotters and in a sugar-citric acid taste solution. The results of this The resultantaroma and taste of Flavors II and III were respectively compared to those of Flavor I on smelling blotters and in prepared pudding by sensory panel techniques. Flavors II and III definitely exhibited definite aroma and taste advantage in comparison with Flavor 1 (Control).

EXAMPLE XIII The flavoring effects of 2-n-butyl-5-methyl-2- oxazoline were investigated in a variety of edible fruit flavored compositions in comparison with controls. Comparison of the flavor effects disclosed that an improvement of the taste or both odor and taste can be attained by incorporating between 5 and 100 ppm of this oxazoline in these compositions. The following tabulation identifies the flavored food composition and the observations made. The levels specified are those at which 2-n-butyl-5-methyl-2-oxazoline was found to give the most desirable effect.

Flavored Substance Level of 2-n-butyl-5- methyl-Z-oxazoline ppm Effects Grape juice Synthetic grape flavored drink (non-carbonated) Apricot juice Synthetic apricot flavored drink Apple jelly Synthetic watermelon flavored drink evaluation revealed that 2-n-butyl-5-methy1-2- oxazoline asserted an enhancement on the aroma and taste at each of the tested levels when compared to the control.

EXAMPLE XII The flavoring effects of 2-n-butyl-5-methyl-2- oxazoline were evaluated at 0, 0.1 and 0.2% in the preparation of synthetic banana flavors, which were prepared as follows:

20 50 Gives to juice a more desirable fresh fruit odor and taste.

5 l5 lmparted a truer and more intense grapy flavor.

l0 25 Contributed with a desirable fruity taste and odor.

15 A more preferred fruit flavor was attained.

5 l5 lntensified the natural fruit flavor. odor and taste. Accented the flavor, odor and taste.

Moreover. it gave a truer and more natural flavor character.

EXAMPLE XIV Beneficial, enhancing effects may be achieved by incorporating 25-100 ppm of the 2-n-butyl-5-methyl-2- oxazoline in perfumed substances including shaving lotions, hand cream, toilet water, perfume extracts, soap, detergents and room deodorizer.

EXAMPLE XV Filter blend tobacco treated with 0, 500 and 2,500

5 ppm of the 2-n-butyl-5-methyl-2-oxazoline was used to prepare cigarettes. The resultant products were evaluated by experienced cigarette smokers. The consensus of the judges was that the tobacco containing 500 and 2,500 ppm of the 2-n-butyl-5-methyl-2-oxazoline exhibited significant improvement in the odor and taste of the tobacco. The untreated control sample was 16 EXAMPLE XXI The following perfume composition is prepared according to accepted procedures:

judged to give a harsh, drier and more pronounced long-lasting after-taste (bitter), while the treated samweight ples exhibited a milder and more desirable tobacco lngredlems Grams odor and taste with a less intense after-taste. Rose Q Bulgarian I I (H0 lorlone Alpha White 0.05 EXAMPLE XVI Vanillin 0.50 Ylang Ylang Oil l.0l Synthenc apple flavor concentrates containing 2-n- Phenyl ethyl Acetate 0.74 pentyl-5-methyl-2-oxazoline were formulated together Clary Sage (French) I 2-N-butyI-S-Methyl-Z-Oxazolme 1.00 with other aromatic chemicals used 1n apple flavors. A Cade Oil 004 negative control formulated apple flavor was used for ghinyl Acggc iAcidc l I (Y 1 0:8

y a moss so ute 0 or ess ugos avia 0. comparative tests. Test results rendered that the lncorphenyl ethyl alcohol I g 5'06 poratlon of 1% to 5% of the 2 n-penty1-5-methyl-2- Diethyl phthalate 10.00 oxazoline to the apple flavor concentrate exhibited a T ta 20.00 more desirable and intense apple flavor than the untreated control.

The aboveformulatlon may be used to perfume tal- EXAMPLE XVII cum powder at a level of from about 0.25 to 0.5% by The procedure described in Example I was repeated Welghtusing a synthetic pineapple flavor concentrate in place of the apple with similar results. EXAMPLE 7 EXAMPLE XVIII The following perfume composition is prepared according to accepted procedures: 2-n-propyl-5-methyl-2-oxazollne at concentratlons of 25% by weight enhances the mint type flavor for dental hygiene products. A blend of clove oil, anethole, lngredifims Weighlin Grams menthol, lemon o1], peppermint oll, Spearmint 0 11, 2 n Ylang Ykmg OH (HO propyl-5-methyl-2-oxazollne and solvent exhlblts a Oil patchuli 0.15 more delicate and preferred flavor when compared a i"; 'f}g with a similar blend which contains no 2-n-propyl-5- yaw yaw methyl 2-oxazoline Cinnamic Aldehyde 0.30 lso-eugenol 0.10 Coumarin 0.50 EXAMPLE XIX Nutmeg O il East Indian 0.15 Two synthetic rum flavors (so-called Rum Punch) gg 'gf ggi' {88 were prepared according to the following prototype Geraniol 110 Benzyl Acetate 1.30 formulations 40 2-N-butyl-5-Methyl-Z-Oxazoline 0.50 Terpinyl Acetate 1.10 Terpineol Prime No. 1 2.30 Imitation Rum Flavor 1 II Total 1000 Acetaldehyde 20.00 20.00 Oil Cognac green 280 2.80 Ethyl butyrate 3.00 3.00 The above formulation may be used to perfume soap Ethyl isovalerate 3.00 3.00 I Aceticwcid 6'00 600 at a concentratlon of from about 0.25 to 0.4% by Oil lemon cold press 4.00 4.00 weight. Rose oil Moroc (l% solution in ethyl alcohol) 2.00 2.00 EXAMPLE XXIII Vanillin 3.00 3.00 v Oil of Cassia redistilled (172 The following perfume composition ls prepared ac- Oil of Cloves USP 0.72 0.72 d. t d d Ethyl oxyhydrate 38.40 38.40 COT mg to acceP e Proce Ethyl alcohol 16.36 3 00 2-ethyl-5-methyl-2-oxazoline 13.36

Total 100.00 100.00 Ingredients Weight in Grams Methyl Anthranilate 0.20 Yara Yara 0.20 I Para-cresyl Acetate v 0.80 The above flavors were used at 0.5% to flavor cake ctmfleuyl Acetate Turklsh Rose 011 0.30 dough. The resultlng baked products wereorganOIep- Geranyl Acetate 1,90 tically evaluated for flavor similarity and flavo r prefer- 60 l -gl-lbutyl-5-methyl-2-oxazoline 8.28 ence. Results of this test showed that Flavor ll (cong f Benzoate taining 2-ethyl-5-methyl-2-oxazollne) were rated to g y te 1.70 I enzyl Formate 2.80 give a more outstanding and preferred flavor than Fla- Yhmg Ylang Oil I v I 300 vol l. Lina Lyl Acetate 4.00 Citronel lol' 1 4,50 EXAMPLE X .lasmimAbsolute v 8.30 Benzyl Acetate V 42.00 The procedure outlined in Example XIX is repro- Llflalool (EX B015 de R086) 25-20 Dlethyl Phthalate 97.00

duced but using a caramel flavor instead of the rum flavor with similar results.

Total 200.00

The above formulation may be employed as a jasmine scent in cologne at a concentration of about 0.5% by weight.

EXAMPLE XXIV The following perfume composition is prepared according to accepted procedures:

Z-N-butyl-S-methyl-2oxazoline Total 125.00

The above formulation may be used as a perfume extract at a concentration of about 1%.

What 1 claim is:

l. A method of flavoring a food base carrying a flavor selected from the group consisting of peanut, cocoa, chocolate, caramel, mint, butter, rum and fruit, said method comprising adding to said base a compound selected from the group consisting of those having the formulae:

R 1 R2 R5 wherein:

R, R'-. R and R are each alkyl groups containing up to 6 carbon atoms; and R and R are each alkyl groups containing from 2 to 6 carbon atoms in an amount sufficient to enhance the flavor and aroma of said food base. 2. The method of claim 1 wherein said compound is 2-isopropyl-4,5-diethyl-3-oxazoline.

3. A method of flavoring a chocolate-flavored base which comprises adding to said base 2-isopropyl-4,5- diethyl-3-oxazoline in an amount sufficient to enhance the flavor and aroma of chocolate. 

1. A METHOD OF FLAVOURING A FOOD BASE CARRYING A FLAVOR SELECTED FROM THE GROUP CONSISTING OF PEANUT, COCOA, CHOCOLATE, CARAMEL, MINT, BUTTER, RUM AND FRUIT, SAID METHOD COMPRISING, ADDING TO SAID BASE A COMPOUND SELECTED FROM THE GROUP CONSISTING OF THOSE HAVING THE FORMULAE,
 2. The method of claim 1 wherein said compound is 2-isopropyl-4, 5-diethyl-3-oxazoline.
 3. A method of flavoring a chocolate-flavored base which comprises adding to said base 2-isopropyl-4,5-diethyl-3-oxazoline in an amount sufficient to enhance the flavor and aroma of chocolate. 